Acetic Acid → HCID 10804488, compound

HRID 1584524Notes

Reaction equation

HRID 1584524 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[S:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C(O)(=O)C.Cl>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([C:19]2[CH2:20][CH2:21][S:16][CH2:17][CH:18]=2)[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 73112,4-Di-tert-butylphenolHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 10804488HCID 10804488, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 17 g (0.082 mol) of 2,4-di-tert-butylphenol, 4.8 g (0.041 mol) of tetrahydrothiopyran-4-one and 5 ml of acetic acid is melted together and is then saturated, with stirring, with hydrochloric acid gas at 40-45° C. After stirring for 12 hours at room temperature, the reaction mixture is diluted with toluene and washed with water, sodium chloride solution and sodium hydrogencarbonate solution. The organic phase is dried over magnesium sulfate and concentrated on a rotary-evaporator. The residue is crystallised from methanol, affording 9.2 g (74%) of 2,4-di-tert-butyl-6-(3,6-dihydro-2H-thiopyran-4-yl)phenol, m.p. 115-119° C. (compound (104), Table 1).

Workup

  1. washwashed with water, sodium chloride solution and sodium hydrogencarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated on a rotary-evaporator
  4. customThe residue is crystallised from methanol

Sources & evidence

ORD record
ord-ffc4dd7cf3a2456c838dabc00fba3b55
Source dataset
uspto-grants-1999_08
Patent number
US05932642

Reaction notes

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